I'm not as keen on blunt as I am open and honest communication while respecting ones feelings; empathizing with them and giving them an avenue to respond without feeling threatened. I think blunt is far too threatening on its own. The idea for me is to make sure that the person I am communicating with feels as comfortable as possible to open up without losing sight of my own needs.
I would suggest using some common and easy communication skills (all adapted from ncv).
1. Observe. Tell him that you notice he texts this woman a lot. You notice his friends opinions are important to him and that he likes to spend time with them. You notice the roomate struggles when you are there.
2. Feelings. Feeling words without putting blame on him. I feel, not you did this to me.
3. Needs. What specifically do you need from him. What do you need for yourself. What do you need to stay in the relationshipEtc.
4. Requests. The actions you would like to see occur. Negotiate boundaries.
5. Have him do this same process so that he might have the space and safety to be able to talk openly and honestly with you.
I would wonder if his friends are making this hard for the situation. Friends who don't understand or even wish to, especially a whole group of them, can be a BIG challenge. Give him the space to express how he feels about his friends and I bet that is the key to his mystery.
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